Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
π Electron Effects on Chemical Shift: Overview01:27

π Electron Effects on Chemical Shift: Overview

An applied magnetic field causes loosely bound π-electrons in organic molecules to circulate, producing a local or induced diamagnetic field over a large spatial volume. As the molecules tumble in solution, the field generated by π-electrons in spherical substituents results in a zero net field. However, the net field generated by π-electrons in non-spherical substituents is not zero. The effect of this induced field depends on the orientation of the molecule with respect to B0, resulting in...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Probing the Ultrafast Photodynamics of Dihydroazulene with In Silico Time-Resolved Photoelectron Spectroscopy and Ultrafast Electron Diffraction.

The journal of physical chemistry. A·2026
Same author

Shedding light on the NN bond: unlocking rapid, catalyst-free direct hydroboration of azoarenes.

Chemical communications (Cambridge, England)·2026
Same author

Visible-Light-Driven Regioselective Di- and Tri-fluoromethylative Benzylation Reaction of 1,1-Diphenylethylenes.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Bis(catecholato)telluranes: Probing Catecholato-Induced Hard Lewis Acidity via Redox-Coupled Halide Abstraction.

Inorganic chemistry·2026
Same author

Twisting Rhodamine─Design of Bright Dyes for Circularly Polarized Fluorescence.

Journal of the American Chemical Society·2026
Same author

Group 14 Substitution as Modulator of Single Molecular Conductance in Highly Conductive Planarized Phenylene-Vinylenes.

Nano letters·2026
Same journal

A Mesopore-Confined and Graphene Oxide-Localized Ruthenium Catalyst Increases Rates of Mid-Chain Polyolefin Hydrogenolysis.

Journal of the American Chemical Society·2026
Same journal

A Type II CDK6 Degrader Enables Cellular Targeting beyond the Limits of Type II Inhibition.

Journal of the American Chemical Society·2026
Same journal

A Guanine Ribonucleotide Atypically Adaptive to the <i>Syn</i> Glycosidic Conformation in a Human Telomeric DNA-TERRA RNA Hybrid G-Quadruplex with (3 + 1) Mixed Strand Orientations Studied by NMR.

Journal of the American Chemical Society·2026
Same journal

A Vakognavine-Type Diterpenoid Alkaloid as FoxO1 Inhibitors against Rheumatoid Arthritis.

Journal of the American Chemical Society·2026
Same journal

Polymeric Hydrogel Interphase Enables Transport-Compatible Fe Stabilization for Hectowatt-Scale Alkaline Water Electrolysis.

Journal of the American Chemical Society·2026
Same journal

Pure Carbon Triggers Nitrogen Reduction: The Critical Role of Spin Electrons Induced at <i>sp</i><sup>3</sup>/<i>sp</i><sup>2</sup> Carbon Interfaces.

Journal of the American Chemical Society·2026
See all related articles
  1. Home
  3. Oriented Electric Field-driven Cis-azobenzene Selective Diborylation Reaction At The Single-molecule Level.
  1. Home
  3. Oriented Electric Field-driven Cis-azobenzene Selective Diborylation Reaction At The Single-molecule Level.

Related Experiment Video

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Oriented Electric Field-Driven Cis-Azobenzene Selective Diborylation Reaction at the Single-Molecule Level.

P A Sreelakshmi1, Reetu Rani Mondal1, Laust Rask2

  • 1Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560012, India.

Journal of the American Chemical Society
|May 20, 2026

View abstract on PubMed

Summary
This summary is machine-generated.

Researchers developed a novel electric field catalysis method for single-molecule cis-azobenzene diborylation reactions. This approach uses intrinsic electric fields in nanocavities, enabling precise control without metal catalysts or light.

More Related Videos

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
10:16

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

Novel Techniques for Observing Structural Dynamics of Photoresponsive Liquid Crystals
10:35

Novel Techniques for Observing Structural Dynamics of Photoresponsive Liquid Crystals

Published on: May 29, 2018

Related Experiment Videos

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
10:16

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

Novel Techniques for Observing Structural Dynamics of Photoresponsive Liquid Crystals
10:35

Novel Techniques for Observing Structural Dynamics of Photoresponsive Liquid Crystals

Published on: May 29, 2018

Area of Science:

  • Synthetic Chemistry
  • Nanocatalysis
  • Physical Chemistry

Background:

  • Developing catalysts with built-in electric fields is crucial for controlling complex chemical reactions.
  • Achieving high stereo- and regioselectivity under mild conditions is a key objective in synthetic chemistry.

Purpose of the Study:

  • To demonstrate a novel approach using intrinsic electric fields within a break junction nanocavity.
  • To trigger and probe substrate-selective, multistep cis-azobenzene diborylation reactions at the single-molecule level.
  • To explore the tuning of reactivity landscapes via external electrical fields in nanometallic junctions.

Main Methods:

  • Utilized a break junction nanocavity to generate an intrinsic electric field.
  • Performed single-molecule cis-azobenzene diborylation reactions in the dark under ambient conditions.
  • Employed theoretical studies to corroborate experimental findings on electric field effects.

    • Main Results:

    • Demonstrated substrate-selective, multistep cis-azobenzene diborylation triggered by the intrinsic electric field.
    • Showcased tuning of the reactivity landscape for "N═N" bond functionalization and borylation via external electrical fields.
    • Confirmed that electric fields reshape the trans-cis-azobenzene isomerization energy landscape, facilitating selective diborylation.

    Conclusions:

    • Electric field catalysis within nanoscale confined environments offers precise control over complex reactions.
    • This method enables selective cis-azobenzene diborylation without metal catalysts or external light irradiation.
    • The study opens new avenues in borylation chemistry through tunable electric field effects.